The present disclosure relates to pyrazinyl carboxamide compounds and their use as fungicides. Fungicides are compounds, of natural or synthetic origin, which act to protect and/or cure plants against damage caused by agriculturally relevant fungi. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.
One embodiment of the present disclosure may include compounds of Formula I:

Wherein R1=H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C(O)R10,
R2=H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, benzyl (in which the phenyl group is optionally substituted with up to three substituents each independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy, C1-C6 haloalkoxy)
R3, R4, R5, and R6 are each independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C(O)R10
X═O, S, N(R7) or (CR8R9)(CR11R12)m(R13R14)n;
m is 0 or 1;
n is 0 or 1;
R7=H, C(O)R10, C1-C6 alkyl, benzyl (in which the phenyl group is optionally substituted with up to three substituents each independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy);
R8 and R9 are each independently H, C1-C6 alkyl, halogen, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;
R10 is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, phenyl or benzyl optionally substituted with up to three substituents each independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy, C1-C6 haloalkoxy);
R11, R12, R13, and R14 are each independently, H, halogen, hydroxyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyl.
Another embodiment of the present disclosure may include a fungicidal composition for the control or prevention of fungal attack comprising the compounds described above and a phytologically acceptable carrier material.
Yet another embodiment of the present disclosure may include a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more of the compounds described above to at least one of the fungus, the plant, the soil, an area adjacent to the plant, and the seed adapted to produce the plant.
The term “alkyl” refers to a branched, unbranched, or cyclic carbon chain, including methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
The term “alkenyl” refers to a branched, unbranched or cyclic carbon chain containing one or more double bonds including ethenyl, propenyl, butenyl, isopropenyl, isobutenyl, cyclohexenyl, and the like.
The term “alkynyl” refers to a branched or unbranched carbon chain containing one or more triple bonds including propynyl, butynyl and the like.
As used throughout this specification, the term ‘R’ refers to the group consisting of C1-C6, C2-C6 alkenyl or C2-C6 alkynyl, unless stated otherwise.
The term “alkoxy” refers to an —OR substituent.
The term “alkoxycarbonyl” refers to a —C(O)—OR substituent.
The term “alkylcarbonyl” refers to a —C(O)—R substituent.
The term “alkylsulfonyl” refers to an —SO2—R substituent.
The term “haloalkylsulfonyl” refers to an —SO2—R substituent where R is fully or partially substituted with Cl, F, I, or Br or any combination thereof.
The term “alkylthio” refers to an —S—R substituent.
The term “haloalkylthio” refers to an alkylthio, which is substituted with Cl, F, I, or Br or any combination thereof.
The term “cyano” refers to a —C≡N substituent.
The term “hydroxyl” refers to an —OH substituent.
The term “amino” refers to a —NH2 substituent.
The term “haloalkoxy” refers to an —OR—X substituent, wherein X is Cl, F, Br, or I, or any combination thereof.
The term “haloalkyl” refers to an alkyl, which is substituted with Cl, F, I, or Br or any combination thereof.
The term “haloalkenyl” refers to an alkenyl, which is substituted with Cl, F, I, or Br or any combination thereof.
The term “haloalkynyl” refers to an alkynyl which is substituted with Cl, F, I, or Br or any combination thereof.
The term “halogen” or “halo” refers to one or more halogen atoms, defined as F, Cl, Br, and I.
The term “hydroxycarbonyl” refers to a —C(O)—OH substituent.
The term “nitro” refers to a —NO2 substituent.
Throughout the disclosure, reference to the compounds of Formula I is read as also including optical isomers and salts of Formula I, and hydrates thereof. Specifically,
when Formula I contains a branched chain alkyl group, it is understood that such compounds include optical isomers and racemates thereof. Exemplary salts include: hydrochloride, hydrobromide, hydroiodide, and the like.
It is also understood by those skilled in the art that additional substitution is allowable, unless otherwise noted, as long as the rules of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity.
Another embodiment of the present disclosure is a use of a compound of Formula I, for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, comprising the application of a compound of Formula I, or a composition comprising the compound to soil, a plant, a part of a plant, roots, foliage, and/or seeds.
Additionally, another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested by a phytopathogenic organism comprising a compound of Formula I and a phytologically acceptable carrier material.